Personalized Travel for Families, Couples & Groups

Love + travel = Wayward Traveling Co.

Hi, I’m Matt, and alongside my wife Amber, we’re the husband-and-wife duo behind Wayward Traveling Co. We’re proud Disney Vacation Experts — and parents of twin newborns — which means we know exactly what it takes to create a magical Disney vacation that works in the real world.

Our clients are families, groups, and couples who want to experience Disney without the overwhelm. We’ve helped parents navigate stroller naps and Lightning Lane strategies, planned unforgettable park days for multi-generational trips, and built itineraries that strike the perfect balance between fun, rest, and making memories.

We believe vacations should be more than a checklist — they should be a story you’ll tell for years. Whether it’s watching your child’s face light up in front of Cinderella Castle, sailing past tropical islands on a cruise, or enjoying a sunset cocktail at a Caribbean all-inclusive, we’re here to make those moments happen.

What We Specialize In

While Disney is our specialty, we also plan:

• Cruises to the Caribbean
• Bahamas, Alaska, and beyond
• All-inclusive resorts in Mexico and the Caribbean
• Universal Orlando Resort vacations
• Group getaways for families, friends, and special celebrations

Why Work With Us

• Real-world experience – We’ve been in the parks with toddlers, navigated crowded holiday weeks, and coordinated large group trips. We’ve stayed in multiple resorts across Disney and the Caribbean, so we give honest, first-hand recommendations.
• Concierge-level planning – We take care of every detail, from park tickets and dining reservations to excursions, transportation, and special events.
• Stress-free booking – Most of our vacations come with zero planning fees, so you can enjoy professional travel planning without extra cost.
• Personal connection – We listen to your needs, customize your trip, and stay in touch before, during, and after your vacation to ensure everything goes smoothly.

A Few Fun Facts About Us

• We’re annual passholders — We visit Disney multiple times a year to keep up with the latest park updates, events, and hidden gems for our clients.
• We’ve traveled as a couple, as a group, and now as a family — We understand how different trip styles require different planning approaches.
• We met through our love of travel — Our first big trip together sealed the deal, and we’ve been exploring the world side-by-side ever since.
• We’ve been “in your shoes” — From navigating airport security with toddlers to handling last-minute weather changes on cruises, we’ve learned the tricks that keep a trip magical no matter what comes your way.

If you’re dreaming of your next Disney adventure — or a cruise, all-inclusive, or group trip anywhere in the world — we’d love to make it happen for you. Let’s turn your travel plans into memories you’ll treasure forever.